SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 13, 2008, Pages 2011-2016

CuI-catalyzed cross-coupling reaction of (E)-vinyl bromides with nitrogen-containing heterocycles

(5) Mao, Jincheng a Hua, Qiongqiong b Guo, Jun a Shi, Daqing a,b Ji, Shunjun a

a SOOCHOW UNIVERSITY (China)

b JIANGSU NORMAL UNIVERSITY (China)

Author keywords

Copper; Cross coupling; Halides; Heterocycles; Nucleophiles

Indexed keywords

BROMIDE; COPPER; NITROGEN; PALLADIUM; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CROSS COUPLING REACTION; SYNTHESIS;

EID: 49649121557 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1077955 Document Type: Article

Times cited : (34)

References (70)

1
- 0003853725
- 7th ed, Akademie: Berlin
- Negwer, M. Organic-Chemical Drugs and their Synonyms: An International Survey, 7th ed.; Akademie: Berlin, 1994.
- (1994) Organic-Chemical Drugs and their Synonyms: An International Survey
- Negwer, M.¹

2
- 84981756782
- (a) Ullmann, F. Ber. Dtsch. Chem. Ges. 1903, 36, 2382.
- (1903) Ber. Dtsch. Chem. Ges , vol.36 , pp. 2382
- Ullmann, F.¹

3
- 0345329013
- (b) Lindley, J. Tetrahedron 1984, 40, 1433.
- (1984) Tetrahedron , vol.40 , pp. 1433
- Lindley, J.¹

4
- 0036589259
- (c) Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
- (2002) Chem. Rev , vol.102 , pp. 1359
- Hassan, J.¹ Sevignon, M.² Gozzi, C.³ Schulz, E.⁴ Lemaire, M.⁵

5
- 33846689629
- (d) Taillefer, M.; Xia, N.; Ouali, A. Angew. Chem. Int. Ed. 2007, 46, 934.
- (2007) Angew. Chem. Int. Ed , vol.46 , pp. 934
- Taillefer, M.¹ Xia, N.² Ouali, A.³

6
- 33746494445
- (e) Schnürch, M.; Flasik, R.; Khan, A. F.; Spina, M.; Mihovilovic, M. D.; Stanetty, P. Eur. J. Org. Chem. 2006, 3283.
- (2006) Eur. J. Org. Chem , pp. 3283
- Schnürch, M.¹ Flasik, R.² Khan, A.F.³ Spina, M.⁴ Mihovilovic, M.D.⁵ Stanetty, P.⁶

7
- 33746174994
- (a) Altman, R. A.; Buchwald, S. L. Org. Lett. 2006, 8, 2779.
- (2006) Org. Lett , vol.8 , pp. 2779
- Altman, R.A.¹ Buchwald, S.L.²

8
- 4143104684
- (b) Antilla, J. C.; Baskin, J. M.; Barder, T. E.; Buchwald, S. L. J. Org. Chem. 2004, 69, 5578.
- (2004) J. Org. Chem , vol.69 , pp. 5578
- Antilla, J.C.¹ Baskin, J.M.² Barder, T.E.³ Buchwald, S.L.⁴

9
- 0037009958
- (c) Antilla, J. C.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 11684.
- (2002) J. Am. Chem. Soc , vol.124 , pp. 11684
- Antilla, J.C.¹ Klapars, A.² Buchwald, S.L.³

10
- 0037149057
- (d) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 2, 581.
- (2002) Org. Lett , vol.2 , pp. 581
- Kwong, F.Y.¹ Klapars, A.² Buchwald, S.L.³

11
- 0034794463
- (e) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727.
- (2001) J. Am. Chem. Soc , vol.123 , pp. 7727
- Klapars, A.¹ Antilla, J.C.² Huang, X.³ Buchwald, S.L.⁴

12
- 0038276941
- (f) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793.
- (2003) Org. Lett , vol.5 , pp. 793
- Kwong, F.Y.¹ Buchwald, S.L.²

13
- 20844435969
- (a) Zhang, H.; Cai, Q.; Ma, D. J. Org. Chem. 2005, 70, 5164.
- (2005) J. Org. Chem , vol.70 , pp. 5164
- Zhang, H.¹ Cai, Q.² Ma, D.³

14
- 0346970774
- (b) Ma, D.; Cai, Q. Synlett 2004, 128.
- (2004) Synlett , pp. 128
- Ma, D.¹ Cai, Q.²

15
- 0141854366
- (c) Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453.
- (2003) Org. Lett , vol.5 , pp. 2453
- Ma, D.¹ Cai, Q.² Zhang, H.³

16
- 0035833707
- (d) Ma, D.; Xia, C. Org. Lett. 2001, 3, 2583.
- (2001) Org. Lett , vol.3 , pp. 2583
- Ma, D.¹ Xia, C.²

17
- 0032501446
- (e) Ma, D.; Zhang, Y.; Yao, J.; Wu, S.; Tao, F. J. Am. Chem. Soc. 1998, 120, 12459.
- (1998) J. Am. Chem. Soc , vol.120 , pp. 12459
- Ma, D.¹ Zhang, Y.² Yao, J.³ Wu, S.⁴ Tao, F.⁵

18
- 0001572402
- Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 5, 4315.
- (2001) Org. Lett , vol.5 , pp. 4315
- Gujadhur, R.K.¹ Bates, C.G.² Venkataraman, D.³

19
- 28044443893
- Liu, L.; Frohn, M.; Xi, N.; Dominguez, C.; Hungate, R.; Reider, P. J. J. Org. Chem. 2005, 70, 10135.
- (2005) J. Org. Chem , vol.70 , pp. 10135
- Liu, L.¹ Frohn, M.² Xi, N.³ Dominguez, C.⁴ Hungate, R.⁵ Reider, P.J.⁶

20
- 34247232757
- Zhu, L.; Cheng, L.; Zhang, Y.; Xie, R.; You, J. J. Org. Chem. 2007, 72, 2737.
- (2007) J. Org. Chem , vol.72 , pp. 2737
- Zhu, L.¹ Cheng, L.² Zhang, Y.³ Xie, R.⁴ You, J.⁵

21
- 28244444924
- Jerphagnon, T.; van Klink, G. P. M.; de Vries, J. G.; van Koten, G. Org. Lett. 2005, 7, 5241.
- (2005) Org. Lett , vol.7 , pp. 5241
- Jerphagnon, T.¹ van Klink, G.P.M.² de Vries, J.G.³ van Koten, G.⁴

22
- 5044231354
- Gajare, A. S.; Toyota, K.; Yoshifuji, M.; Ozawa, F. Chem. Commun. 2004, 1994.
- (1994) Chem. Commun , vol.2004
- Gajare, A.S.¹ Toyota, K.² Yoshifuji, M.³ Ozawa, F.⁴

23
- 33646096265
- Zhang, Z.; Mao, J.; Zhu, D.; Wu, F.; Chen, H.; Wan, B. Tetrahedron 2006, 62, 4435.
- (2006) Tetrahedron , vol.62 , pp. 4435
- Zhang, Z.¹ Mao, J.² Zhu, D.³ Wu, F.⁴ Chen, H.⁵ Wan, B.⁶

24
- 49649100297
- (a) Xu, L.; Mao, J.; Zhu, D.; Wu, F.; Wang, R.; Wan, B. Tetrahedron 2006, 61, 6553.
- (2006) Tetrahedron , vol.61 , pp. 6553
- Xu, L.¹ Mao, J.² Zhu, D.³ Wu, F.⁴ Wang, R.⁵ Wan, B.⁶

25
- 33745611095
- (b) Zhu, D.; Xu, L.; Wu, F.; Wan, B. Tetrahedron Lett. 2006, 47, 5781.
- (2006) Tetrahedron Lett , vol.47 , pp. 5781
- Zhu, D.¹ Xu, L.² Wu, F.³ Wan, B.⁴

26
- 0042347800
- (a) Lu, Z.; Twieg, R. J.; Huang, S. D. Tetrahedron Lett. 2003, 44, 6289.
- (2003) Tetrahedron Lett , vol.44 , pp. 6289
- Lu, Z.¹ Twieg, R.J.² Huang, S.D.³

27
- 11144351034
- (b) Lu, Z.; Twieg, R. J. Tetrahedron 2005, 61, 903.
- (2005) Tetrahedron , vol.61 , pp. 903
- Lu, Z.¹ Twieg, R.J.²

28
- 0037201095
- (a) Kelkar, A. A.; Patil, N.M.; Chaudhari, R. V. Tetrahedron Lett. 2002, 43, 7143.
- (2002) Tetrahedron Lett , vol.43 , pp. 7143
- Kelkar, A.A.¹ Patil, N.M.² Chaudhari, R.V.³

29
- 9644277114
- (b) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337.
- (2004) Coord. Chem. Rev , vol.248 , pp. 2337
- Beletskaya, I.P.¹ Cheprakov, A.V.²

30
- 25444463074
- Rao, H.; Fu, H.; Jiang, Y.; Zhao, Y. J. Org. Chem. 2005, 70, 8107.
- (2005) J. Org. Chem , vol.70 , pp. 8107
- Rao, H.¹ Fu, H.² Jiang, Y.³ Zhao, Y.⁴

31
- 0038276941
- Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793.
- (2003) Org. Lett , vol.5 , pp. 793
- Kwong, F.Y.¹ Buchwald, S.L.²

32
- 33846195911
- (a) Jiang, D.; Fu, H.; Jiang, Y.; Zhao, Y. J. Org. Chem. 2007, 72, 672.
- (2007) J. Org. Chem , vol.72 , pp. 672
- Jiang, D.¹ Fu, H.² Jiang, Y.³ Zhao, Y.⁴

33
- 33750033596
- (b) Xie, Y.; Pi, S.; Wang, J.; Yin, D.; Li, J. J. Org. Chem. 2006, 71, 8324.
- (2006) J. Org. Chem , vol.71 , pp. 8324
- Xie, Y.¹ Pi, S.² Wang, J.³ Yin, D.⁴ Li, J.⁵

34
- 9244225109
- (c) Cristau, H. J.; Cellier, P. P.; Spindler, J. F.; Taillefer, M. Chem. Eur. J. 2004,10, 5607.
- (2004) Chem. Eur. J , vol.10 , pp. 5607
- Cristau, H.J.¹ Cellier, P.P.² Spindler, J.F.³ Taillefer, M.⁴

35
- 35948940756
- (d) Ma, H.-C.; Jiang, X.-Z. J. Org. Chem. 2007, 72, 8943.
- (2007) J. Org. Chem , vol.72 , pp. 8943
- Ma, H.-C.¹ Jiang, X.-Z.²

36
- 36049007571
- In addition, the copper-catalyzed C-N couplings performed at room temperature have been reported
- (e) Yang, M.; Liu, F. J. Org. Chem. 2007, 72, 8969. In addition, the copper-catalyzed C-N couplings performed at room temperature have been reported:
- (2007) J. Org. Chem , vol.72 , pp. 8969
- Yang, M.¹ Liu, F.²

37
- 33745962425
- (f) Shafir, A.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 8742.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 8742
- Shafir, A.¹ Buchwald, S.L.²

38
- 34248588689
- (g) Lv, X.; Bao, W. J. Org. Chem. 2007, 72, 3863.
- (2007) J. Org. Chem , vol.72 , pp. 3863
- Lv, X.¹ Bao, W.²

39
- 9244225109
- (a) Cristau, H. J.; Cellier, P. P.; Spindler, J. F.; Taillefer, M. Chem. Eur. J. 2004, 10, 5607.
- (2004) Chem. Eur. J , vol.10 , pp. 5607
- Cristau, H.J.¹ Cellier, P.P.² Spindler, J.F.³ Taillefer, M.⁴

40
- 20844435969
- (b) Zhang, H.; Cai, Q.; Ma, D. J. Org. Chem. 2005, 70, 5164.
- (2005) J. Org. Chem , vol.70 , pp. 5164
- Zhang, H.¹ Cai, Q.² Ma, D.³

41
- 33646058038
- (c) Lv, X.; Wang, Z.; Bao, W. Tetrahedron 2006, 62, 4756.
- (2006) Tetrahedron , vol.62 , pp. 4756
- Lv, X.¹ Wang, Z.² Bao, W.³

42
- 33646192747
- (d) Rao, H.; Jin, Y.; Fu, H.; Jiang, Y.; Zhao, Y. Chem. Eur. J. 2006, 12, 3636.
- (2006) Chem. Eur. J , vol.12 , pp. 3636
- Rao, H.¹ Jin, Y.² Fu, H.³ Jiang, Y.⁴ Zhao, Y.⁵

43
- 33750033596
- (e) Xie, Y.; Pi, S.; Wang, J.; Yin, D.; Li, J. J. Org. Chem. 2006, 71, 8324.
- (2006) J. Org. Chem , vol.71 , pp. 8324
- Xie, Y.¹ Pi, S.² Wang, J.³ Yin, D.⁴ Li, J.⁵

44
- 28044443893
- (f) Liu, L.; Frohn, M.; Xi, N.; Dominguez, C.; Hungate, R.; Reider, P. J. J. Org. Chem. 2005, 70, 10135.
- (2005) J. Org. Chem , vol.70 , pp. 10135
- Liu, L.¹ Frohn, M.² Xi, N.³ Dominguez, C.⁴ Hungate, R.⁵ Reider, P.J.⁶

45
- 34248547200
- (g) Verma, A. K.; Sing, J.; Sankar, V. K.; Chaudhary, R.; Chandra, R. Tetrahedron Lett. 2007, 48, 4207.
- (2007) Tetrahedron Lett , vol.48 , pp. 4207
- Verma, A.K.¹ Sing, J.² Sankar, V.K.³ Chaudhary, R.⁴ Chandra, R.⁵

46
- 0036304013
- The selected examples: (a) Kurdaziel, K.; Glowiak, T. J. Coord. Chem. 2002, 55, 327.
- The selected examples: (a) Kurdaziel, K.; Glowiak, T. J. Coord. Chem. 2002, 55, 327.

47
- 0141618307
- (b) Branowska, D. Synthesis 2003, 2096.
- (2003) Synthesis , pp. 2096
- Branowska, D.¹

48
- 49649119795
- (c) Aggarwal, V. K.; De Vicente, J.; Bonnert, R. V. J. Org. Chem. 2003, 68, 5119.
- (2003) J. Org. Chem , vol.68 , pp. 5119
- Aggarwal, V.K.¹ De Vicente, J.² Bonnert, R.V.³

49
- 0037024158
- (d) Mano, N.; Kim, H. H.; Zhang, Y.; Heller, A. J. Am. Chem. Soc. 2002, 124, 6480.
- (2002) J. Am. Chem. Soc , vol.124 , pp. 6480
- Mano, N.¹ Kim, H.H.² Zhang, Y.³ Heller, A.⁴

50
- 0025129410
- (e) Morita, T.; Nozawa, Y. Nippon Ishinkin Gakkai Zasshi 1990, 31, 363.
- (1990) Nippon Ishinkin Gakkai Zasshi , vol.31 , pp. 363
- Morita, T.¹ Nozawa, Y.²

51
- 0033588015
- (a) Tzalis, D.; Henkelmann, J.; Heider, M. Tetrahedron Lett. 1999, 40, 6193.
- (1999) Tetrahedron Lett , vol.40 , pp. 6193
- Tzalis, D.¹ Henkelmann, J.² Heider, M.³

52
- 0035842527
- (b) Hayat, S.; Rahman, A.; Choudhary, M. I.; Khan, K. M.; Schumann, W.; Bayer, E. Tetrahedron 2001, 57, 9951.
- (2001) Tetrahedron , vol.57 , pp. 9951
- Hayat, S.¹ Rahman, A.² Choudhary, M.I.³ Khan, K.M.⁴ Schumann, W.⁵ Bayer, E.⁶

53
- 0035858723
- (c) Lam, P. Y. S.; Vincent, G.; Clark, C. G.; Deudon, S.; Jadhav, P. K. Tetrahedron Lett. 2001, 42, 3415.
- (2001) Tetrahedron Lett , vol.42 , pp. 3415
- Lam, P.Y.S.¹ Vincent, G.² Clark, C.G.³ Deudon, S.⁴ Jadhav, P.K.⁵

54
- 37049139374
- (d) Cooper, G.; Irwin, W. J. J. Chem. Soc., Perkin Trans, 1 1975, 798.
- (1975) J. Chem. Soc., Perkin Trans, 1 , pp. 798
- Cooper, G.¹ Irwin, W.J.²

55
- 37049098379
- (e) Cooper, G.; Irwin, W. J. J. Chem. Soc., Perkin Trans, 1 1976, 545.
- (1976) J. Chem. Soc., Perkin Trans, 1 , pp. 545
- Cooper, G.¹ Irwin, W.J.²

56
- 0002261207
- Lebedev, A. Y.; Izmer, V. V.; Kazyul'kin, D. N.; Beletskaya, I. P.; Voskoboynikov, A. Z. Org. Lett. 2002, 4, 623.
- (2002) Org. Lett , vol.4 , pp. 623
- Lebedev, A.Y.¹ Izmer, V.V.² Kazyul'kin, D.N.³ Beletskaya, I.P.⁴ Voskoboynikov, A.Z.⁵

57
- 33745908283
- Taillefer, M.; Ouali, A.; Renard, B.; Spindler, J.-F. Chem. Eur. J. 2006,12, 5301.
- (2006) Chem. Eur. J , vol.12 , pp. 5301
- Taillefer, M.¹ Ouali, A.² Renard, B.³ Spindler, J.-F.⁴

58
- 21344443884
- Wang, Z.; Bao, W.; Jiang, Y. Chem. Commun. 2005, 2849.
- (2005) Chem. Commun , pp. 2849
- Wang, Z.¹ Bao, W.² Jiang, Y.³

59
- 37649014351
- (a) Mao, J.; Guo, J. Tetrahedron 2008, 64, 1383.
- (2008) Tetrahedron , vol.64 , pp. 1383
- Mao, J.¹ Guo, J.²

60
- 33747365655
- (b) Zhu, D.; Wang, R.; Mao, J.; Xu, L.; Wu, F.; Wan, B. J. Mol. Catal. A: Chem. 2006, 256, 256.
- (2006) J. Mol. Catal. A: Chem , vol.256 , pp. 256
- Zhu, D.¹ Wang, R.² Mao, J.³ Xu, L.⁴ Wu, F.⁵ Wan, B.⁶

61
- 0000666195
- Chowdhury, S.; Roy, S. J. Org. Chem. 1997, 62, 199.
- (1997) J. Org. Chem , vol.62 , pp. 199
- Chowdhury, S.¹ Roy, S.²

62
- 49649083923
- General Procedure for C-N Coupling Reactions of β-Bromostyrene and Heterocycle Copper(I) iodide (0.1 equiv) and Cs2CO 3 (2.0 equiv) were added to a screw-capped test tube. The tube was then evacuated and backfilled with argon (3 cycles, N,N- Dimethylformamide (2 mL, nitrogen-containing heterocycles (1.2 equiv; if liquid) and vinyl halide (1.0 equiv; if liquid) were added by syringe at r.t. The tube was again evacuated and backfilled with argon 3 cycles, The mixture was heated to 120 °C and stirred for 36-50 h. After cooling to r.t, the mixture was diluted with H2O, and the combined aqueous phases were extracted three times with EtOAc. The organic layers were combined, dried over Na2SO4, and concentrated to yield the crude product, which was further purified by silica gel chromatography, using PE and EtOAc as eluents to provide the desired product. Characteristic Data of Representative Products Com
- + + H]: 249.1154; found: 249.1153.

63
- 33845227375
- 4NBr as the phase-transfer catalyst: Chang, J. W. W.; Xu, X.; Chan, P. W. H. Tetrahedron. Lett. 2007, 48, 245.
- 4NBr as the phase-transfer catalyst: Chang, J. W. W.; Xu, X.; Chan, P. W. H. Tetrahedron. Lett. 2007, 48, 245.

64
- 37349108522
- 2O-catalyzed N-arylation of nitrogen nucleophiles: Correa, A.; Bolm, C. Adv. Synth. Catal. 2007, 349, 2673.
- 2O-catalyzed N-arylation of nitrogen nucleophiles: Correa, A.; Bolm, C. Adv. Synth. Catal. 2007, 349, 2673.

65
- 35548982667
- Cul-catalyzed N-arylation of nitrogen nucleophiles with aryl halides: Zhu, L.; Guo, P.; Li, G.; Lan, J.; Xie, R.; You, J. J. Org. Chem. 2007, 72, 8535.
- (c) Cul-catalyzed N-arylation of nitrogen nucleophiles with aryl halides: Zhu, L.; Guo, P.; Li, G.; Lan, J.; Xie, R.; You, J. J. Org. Chem. 2007, 72, 8535.

66
- 0035806285
- (Z)-β-Bromostyrene was synthesized according the references: (a) Kuang, C.; Senboku, H.; Tokuda, M. Tetrahedron Lett 2001, 42, 3893.
- (Z)-β-Bromostyrene was synthesized according the references: (a) Kuang, C.; Senboku, H.; Tokuda, M. Tetrahedron Lett 2001, 42, 3893.

67
- 19344365167
- (b) Kuang, C.; Yang, Q.; Senboku, H.; Tokuda, M. Tetrahedron 2005, 61, 4043.
- (2005) Tetrahedron , vol.61 , pp. 4043
- Kuang, C.¹ Yang, Q.² Senboku, H.³ Tokuda, M.⁴

68
- 49649097796
- 3): δ = 7.68 (d, J = 7.2 Hz, 1 H, ArH), 7.30-7.40 (m, 3 H, ArH), 7.06 (d, J = 8.0 Hz, 1 H, CH=CHPh), 6.42 (d, J = 8.0 Hz, 1 H, CH=CHPh).
- 3): δ = 7.68 (d, J = 7.2 Hz, 1 H, ArH), 7.30-7.40 (m, 3 H, ArH), 7.06 (d, J = 8.0 Hz, 1 H, CH=CHPh), 6.42 (d, J = 8.0 Hz, 1 H, CH=CHPh).

69
- 49649083924
- 3): 6 = 137.4, 134.1, 130.0, 129.1, 128.9, 128.7, 123.8, 122.8, 118.9.
- 3): 6 = 137.4, 134.1, 130.0, 129.1, 128.9, 128.7, 123.8, 122.8, 118.9.

70
- 34248547200
- Verma, A. K.; Singh, J.; Sankar, V. K.; Chaudhary, R.; Chandra, R. Tetrahedron Lett. 2007, 48, 4207.
- (2007) Tetrahedron Lett , vol.48 , pp. 4207
- Verma, A.K.¹ Singh, J.² Sankar, V.K.³ Chaudhary, R.⁴ Chandra, R.⁵

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.